The Education of The Dorkiest and Most Adorable Couple in Pawnee
by myfriendfiction
Summary: Leslie and Ben had a lot to learn about themselves before they were ready to find each other. They did a lot of wandering around until they met each other. And then, it was history, they became the dorkiest and most adorable couple in town. In the state. Probably the world. (Definitely.) Take a look back at the people and relationships that paved the way.
1. The Education of Leslie Knope Part I

The Education of The Dorkiest and Most Adorable Couple in Pawnee

 _Leslie and Ben had a lot to learn about themselves; what they needed, wanted, and desired before they were ready to find each other. They did a lot of wandering around until they met each other. And then, it was history, they became the dorkiest and most adorable couple in town. In the state. Probably the world. (Definitely.) Take a look back at the people and relationships that paved the way for them to find each other._

The Education of Leslie Knope Part I

JJ Wyszynski\- He had the bluest eyes and the biggest smile in the entire preschool class. He was great at sharing his toys. Leslie sat next to him at Blue Table. Leslie let him borrow her crayons and declared that he was her boyfriend. He accepted and at lunch she brought him a special cookie she had baked. A few days later during recess they started playing tag. Leslie was "it". She decided she was going to get JJ first, even though he was the farthest away from her. She caught him rather quickly and wanted him to tag her next. This went on all week during recess. On Friday JJ let Leslie know that he didn't like that she always wanted to tag him first. JJ said that Leslie wasn't fun to play tag with. He borrowed another girl's crayons from that point on. Leslie decided that she could find plenty of other people that would let her be "it" during tag and would be fun to catch.

Opie Gurdson- Opie was Leslie's crush for 4th grade and into 5th grade. He was funny and always made her laugh. He made good grades and was nice to all the other kids. He and Leslie became really good friends; eating lunch together, playing at PE together, meeting at the Park after school, teaming up on projects, and even hanging out at each other's houses. Leslie thought that surely Opie would ask her to be his girlfriend. Then, at a slumber party, Gretchen Johannson told the girls at the party that Opie had asked her to be his girlfriend and she needed help replying to his note. Leslie's heart broke as she helped Gretchen draft the note. Of course, towards the middle of 5th grade Leslie dad had become very sick and Opie became a distant memory.

Willy Carlson\- Willy and Leslie were in the math club and student council together. They studied together and sat next to each other on the bus on the way to meets. Leslie developed a huge crush on Willy. He was a pretty popular guy. He was on the middle school's basketball team. They began to talk on the phone about stuff other than math. Leslie couldn't wait to finish her homework everyday so that she could call Willy. Leslie would enthusiastically wave at Willy whenever she saw him at school. She baked him special cookies in the shape of basketballs and the mathematical pi symbol. She took it upon herself to sit at his lunch table with him and the other basketball players. Leslie started to notice that Willy seemed to be cutting their phone calls short and he stopped acknowledging her in the hallway. He also started sitting with Fred Johnson on the bus on the way to math meets. Fred was always sweaty and whispered to himself constantly. Leslie decided that she needed to try to spend more time with Willy that way he would know that she liked him and ask her to go out with him. A few weeks later Willy got down on one knee in the middle school hallway and begged Leslie to never call him again. And to never talk to him in person as well.

Jeremiah Finkle\- Jeremiah sat behind Leslie in 9th grade history. He'd often asked to borrow a pencil or paper. He'd ask her opinion on a subject before getting to work. He even picked Leslie first for group projects. Leslie thought that really meant something. So she asked him out on a date. It probably should've been a clue when his response was, "Yeah. Okay. You're not bad looking. You are blonde, so, okay." They dated for a few months. He was her first kiss and first make out partner (37 seconds counts as making out, right? Leslie counted. In retrospect they probably would've made out more if Leslie hadn't talked so much and her mind hadn't been occupied by counting how long kisses and making out had lasted.) Leslie always made sure to find Jeremiah at lunch, sit by him at the bus stop, bring him desserts at least five times a week, and call him every day before bed. After their three month anniversary Leslie received a call from Jeremiah's mom telling Leslie that Jeremiah was effectively breaking up with Leslie.

Harvey Pierson\- Harvey was a nice guy. He was smart, in the AV Club, and a huge dork that was bullied quite a bit. While Leslie was busy crushing on other guys Harvey was crushing on her. Leslie had accomplished a lot during her high school career. She hadn't had a lot of time for guys and she was mostly fine with that. But prom was coming up and all her friends had dates but her. Her Angela Lansbury haircut had finally grown out. Her friends said that may have deterred guys but Leslie thought that was crazy. Angela Lansbury was amazing. When Leslie wasn't asked to prom, a few weeks out from it happening, the prom that she had planned, Harvey nervously asked her and she accepted on the condition that he understood that she would be busy much of the night as she was in charge of the prom. He understood. They went out a few times before prom and Leslie learned that Harvey was really nice, he could make her laugh (sometimes- she just didn't get his interest in Claymation though), and he treated her great. The only thing that made Leslie unsure was that he wore 3D glasses to the date and they did not see a 3D movie. They went bowling and Harvey wasn't at all upset that Leslie had beat him by a very wide margin. At prom it turned out that Harvey was a pretty fun person to dance with though he did step on her toes a lot. They had a great night and Leslie considered going down the root that everyone seemed to be looking forward to after prom, hooking up. But Leslie just wasn't attracted to Harvey. They made out but she wasn't sure if he had gotten to second base on purpose or on accident. Things kind of just fizzled out in the hectic weeks that led to graduation. A few weeks after prom Leslie heard that Harvey got electrocuted by a VCR and legend has it that he can walk by a microwave and it will turn on.

Lester Sicovitaliz the Third\- Freshman year at college Leslie met Lester in her political science class. She admired his thoughts on the role of government. They had terrific discussions and a few heated debates on Egyptian debt relief and NAFTA. He was called "Socialist Sicovitaliz". Their longest make out was 57 seconds after which he took a hand from his asthma inhaler. He was a rather slobbery kisser but Leslie figured practice would make perfect and he had great lips to practice with. He visited Pawnee once with Leslie and they took a biscuit class together and after he French kissed her because they had made French biscuits. They also engaged in some over the clothes touching in his Toyota Corolla and nothing embarrassing had happened like it did when Leslie had gotten within five inches of Harvey's "private parts". Poor Harvey. Lester and Leslie had never had the "we're dating exclusively talk" but Leslie naively assumed that if you made out with someone you didn't need to have the talk. One day Leslie met Lester at a local park to lend him her history flashcards. Leslie walked upon a lovely picnic with wine and flowers set up and smiled. As she began to sit down Lester said, "Don't eat anything! Rebecca's coming." "Whose Rebecca?" Rebecca was known as "Capitalist Conniver Rebecca" and apparently the two had been having a heated argument and one thing led to another….and they were crazy about each other and according to Lester he and Leslie weren't exclusive anyway.

David Elinor\- Sophomore year Leslie met David Elinor. David looked like the "All American" boy. Blonde hair, blue eyes, boyish grin. He was outgoing and a great student. While he didn't look like Robert Redford, he did look like a young Robert Redford, which wasn't a bad thing. Leslie was smitten. She felt bold. And when her roommate, who was dating one of David's friends, told her that David had asked if she was single, Leslie created a binder, which led to her enacting the binder she had created, "Ask out All American Boy Genius Protocal." The plan involved baked goods, an extra ticket to a museum he just had to take off her hands and oh yes, I'd love to go with you. As well as, a singing telegraph to wish him luck on a test, back rubs, "randomly bumping into him" multiple times, and the grand finale….skywriting, which displayed, "Will you go out on a date with me, David Elinor? This is from Leslie Knope in your Computer Coding Class. She sits two rows in front of you and sits at the same group as you in Biology." He said yes. On their first date Leslie thought she was drinking terrible wine. When she only had a sip left she figured out that she was drinking vinegar. On their third date Leslie reached over the table to point at a dish on David's menu and her sleeve caught fire. None of those embarrassing events made David run away screaming. Leslie had decided that just because she had went to such great efforts to ask him out it didn't mean the effort should stop just because they were dating. So the baked good, gifts, and surprises continued. David would tell her it was sweet but it was too much and she should stop. They had some great dates and went all the way to third base, more than a few times and said "I love you." Leslie thought David was more experienced than her and she pretended she was also experienced. Luckily, David saw through her nervous eagerness. Leslie thought that David would be the one, as she called it, to first "make love with". But time was not on their side. Eventually, after a massive amount of miscommunication and a lot of steamrolling Leslie received a message via skywriting which stated, "I just can't be with you anymore. It is too much. I'm breaking up with you Leslie Knope. I'm sorry. This is final. Sincerely, David Elinor.

Billy Berman- Billy and Leslie had met Freshman year but started getting close Junior year of college. He was nice, they had similar interests, and got along well. Billy was really smart and Leslie thought he could be a senator one day. Billy just saw politics as a hobby and not a career path. Billy thought career politicians were a corrupt bunch and he thought there should be term limits. Leslie gave many passionate speeches as to why that wasn't true. He enjoyed politics but was rather cynical. On a trip with friends to Lake Michigan while scuba diving Leslie told Billy that she loved him. He shot up and got the bends. He then broke up with her on the boat back to shore saying that they hadn't been together that long and it was just too soon. A few hours later he knocked on her motel door and apologized. Billy told Leslie she was a great girl and he'd be crazy not to love her. "So, I do love you. I'm sorry I freaked out. Will you take me back?" Leslie accepted. They had been dating for three months when Leslie decided to have sex for the first time. It was the first time for both and Leslie felt confused afterwards. It wasn't what she had expected. She thought it might be a transforming experience. Instead Leslie realized that she had eaten brownies that were far more exciting than sex. Billy lived in a small town in Kentucky that was only a few hours away from Pawnee so Leslie went to planning, binder style, determined to keep the relationship going over the summer. He had a summer job and Leslie was volunteering as a counselor yet again for Pawnee's Recreational Summer Programs. They met only once that summer at a half way point. Leslie could then check car sex on a country road surrounded by corn fields off her list, which is called the Midwest Special. While their sex life wasn't in competition with that one amazing brownie Leslie had eaten freshman year it had significantly improved. After that there was the rest of summer to contend with resulting in missed phone calls and short messages. By the end of summer Billy told Leslie over the phone that he thought they should breakup and see other people and he hoped they could be friends senior year. Senior year brought nothing deeper than some small talk and waves between them. Anyway, Leslie had no time for guys as she completed her internships and senior year of college. After graduating from college Leslie enrolled in a master's program.

Keith, Steve, Matt, Mike, Gil\- After graduating from college Leslie stayed in Bloomington to get her master's degree. Leslie's roommate implored Leslie to jump into dating and have some fun. She went on a blind date with a guy named Keith where she tripped over a tree root during a walk in a park. She broke her leg. While waiting for the ambulance Keith said he "wasn't feelin it" and that was the end of that. There was a night at a local college bar where Leslie got the number for a really cute guy, Steve, and later called him. She was then informed that he wasn't looking for a date, just a woman to clean his house. Leslie understood how he made the mistake. It probably wasn't good to have a conversation about window cleaner at a bar. Leslie had been the one to bring it up in an attempt to start up a conversation. Leslie got a huge crush on Matt Milkleson in her Young Deomcrats Club. Leslie came on really strong after the two had spent an entire evening at a party talking. Matt told her he was gay but that if he was straight he'd be freaked out by her enthusiasm and she needed to tone it down a notch or twelve. He did take her shopping and teach her how to wear eyeliner. Leslie had her first one night stand with Mike Lipiniki, it left her feeling rather awkward. She also went on date with Gil Gilbert, a pre law student she met when interning at an EPA office in Indianapolis. They went to a movie together. It was super boring and Leslie was exhausted after barely sleeping for a week as she wrapped herself up in planning her childhood best friend's baby shower, her job as tour guide, her master's classes, and her internship. She fell asleep. When she woke up his hands were in her mouth. They went on two dates after that. Then Leslie stopped answering his phone calls because he kept asking to see her feet.

Nathan Milfordson\- After getting her master's degree Leslie wanted to move back to Pawnee and start the next phase of her life plan. Leslie was homesick while away at college and while everyone else at school had dreamed of broadening their horizons Leslie dreamed of moving back home. She wanted to work at the Parks Department in City Hall, get married at the gazeebo in Ramset Park and raise her children to love Lil Sebastian. In due time she would become mayor, then governor, and ultimately president and then write her autobiography. She could have gotten a job at the university, a museum, or with the state or the city of Indianapolis or Bloomington. Instead Leslie moved back home. While she waited for a job to open up at city hall she worked at the Pawnee and the Wamapoke Historical Societies. Leslie had met Nathan, who had just started as working in admissions at Pawnee Community College. Leslie's relationship with Nathan was pretty easy. They dated for about a year and a half. The only issue was that he didn't seem to want to talk about the future of their relationship much. He didn't seem very committed. But Leslie had heard her friends talk about how they had to goad their guys in to commitment and marriage and having kids. As Leslie does with everything she put her soul into the relationship. She tried to do what Oprah said you should do in a relationship (she missed Oprah's show about men that don't want to commit and not trying to change your man) and she tried to implement Good Housekeeping's advice about keeping your relationship fun. Leslie had been working on these things really hard lately because they had been together for a year and a half and she thought they should be going after the next step, moving in together. So in the spirit of fun Leslie hopped into the shower to surprise Nathan. He broke up with her by saying, "Leslie,shhhhhhh. Can you just be quiet for one minute? I have been trying to get this out but you keep talking and doing stuff and….I think we should breakup. To clarify, we're breaking up," Nathan said and then left Leslie alone in the shower. Wet. With shampoo in her hair. It was his shower. His roommate banged on the door three minutes later telling her to hurry up as he had to "take a waz." Leslie was rather devastated. She threw herself into her work and just a few weeks later a job in the Parks and Rec department opened up. Leslie got a chance to take a breath and she realized that she really didn't even miss Nathan. She more missed the idea of Nathan and being in a relationship. Leslie learned that life didn't go according to plan. While her friends from growing up might be married and have kids she might have to wait. And she didn't want the kind of relationship they had with their husbands and boyfriends. She didn't want to have to manipulate anyone or wait for them to change. She realized that Nathan didn't really respect her. The way he broke up with her was a sign but also he didn't listen to her, he didn't smile when she walked into the room, he didn't share her values or compliment her.

Clark Beaumont\- Leslie met Clark at a Civil War reenactment she was staging in Pawnee. It was her first big Parks&Rec project that she was lead on. It was a three day event. Friday it was staged for local school field trips and Saturday and Sunday was for the public. Clark was from Louisville and was the first to sign up. He came armed with Civil War puns. That won Leslie over. Leslie thought she was madly in love. She couldn't stop thinking about him and her friend and coworker Lindsey Carlisle Shay encouraged her. She asked Clark out for dinner after the ceremony. He drove a motorcycle with a side car. In spite of the side car Leslie was riding in detaching they had a great time and met up a few more times in the coming weeks. Leslie would often call him but the conversations seemed rather one sided and would end abruptly. Leslie tried to remember why Oprah said that was a warning sign. Every time she and Clark met up he came dressed in his civil war reenactment clothes. Leslie told herself he was just passionate about his hobby but it was rather strange to eat seafood with someone wearing a Civil War uniform. Leslie ended things after Clark's wife answered the phone and cursed her out.

Tom Kent\- Leslie's mom set her up on a date with Tom Kent. Her mom claimed that he needed a nice woman. He had a stable job, came from a good family, was newly divorced, and had two great kids and that Leslie wasn't getting any younger. "I married your father straight out of college." Leslie went on a few dates with him but he talked about his ex wife the entire time. Leslie gently rejected him.

Mark Brandanowitz\- Mark had become Leslie's first friend at city hall. Leslie had been sent off to get some office supplies and to fax something. Ron had just grunted the instructions at her and Donna was at lunch so Leslie set off to figure out what to do. She had walked into Mark and dropped her papers. Mark helped her pick them up and showed her a fax machine she could use and where to get office supplies. He also gave her a tour of the building, which Leslie didn't really need because her mom worked there but she couldn't resist. She confessed after she corrected him on a few facts. He seemed impressed by her knowledge. Over lunches and cups of coffee Leslie came to admire Mark. He listened to what she had to say and he smiled when she said hello to him. He made her feel like she was capable of achieving her goals and dreams. So when one drunken night Mark made a pass at her she took him back to her place and they slept together. Mark had been rather, giving, or so Leslie thought at the time. After Mark had fallen asleep Leslie thought about their relationship. It was a great story-they literally met when she dropped papers in the hallway. It was like the start of a romantic comedy. She felt amazing. In the morning she asked Mark if he remembered how they had met. He didn't. He said he hoped things wouldn't be awkward since he loved working with Leslie and looked forward to hanging out with her. He said they should stay friends and he didn't want to risk ruining their friendship with a romantic relationship. Leslie was so excited about this chain of events that it couldn't kill her buzz. Leslie held onto her work crush on Mark for six years. She longed for him to notice her, appreciated how he listened to her and made her feel like she could accomplish her goals. But eventually Leslie realized that Mark, while he encouraged and helped her, he didn't think she could overcome any and every obstacle. He could support her but he could never stand next to her and fight with her.

Dr. Hermanstein\- He was an amazing dentist. She had never had a man be so gentle and praiseful. He was twelve years her senior. They dated for 4 months during Leslie's 6 year crush on Mark. The doctor was considerate and smart but he talked about dentistry in the bedroom too much. His skills did not parlay into the bedroom only making Leslie's night with Mark become bigger in her head. Leslie tried to surprise him one time but dressing up in "sexy scrubs" and acting like a dental hygienist. He broke up with her right then and there claiming they were incompatible. He stated, "Why would I want to be reminded of being a dentist when I'm at home?" Her six month dental checkup was a bit awkward but he was an amazing dentist. In a strange twist he ended up closing down his dental practice as he couldn't compete with Dr. Jamm's low prices.

Sam Kettleman- Sam was a water guy and Leslie tipsily made out with him once. They talked on the phone a few times but Leslie ended up yelling at him when he expressed his negative feelings about the government. He hung up on her.

Vilcrest Pandermine\- Vilcrest was a high level employee at Kernstein's Nipple Factory Leslie's aunt and cousin set her up with. They said he was a really friendly guy, had a full head of hair, and a nice economical car. Leslie arrived at restaurant first. Vilcrest arrived a few minutes later- with another woman. Leslie made up an excuse,that her dog Mr. Barkley needed to go to a meeting, when she realized the other woman was there to stay.

Geroge Gernway- Leslie thought her mother was setting her up for a government connection. It was actually a date with a senior citizen. It didn't work out.

Dave Sanderson\- While Dave did not know who Madeline Albright was he was willing to learn. That meant a lot to Leslie. Things with Dave were nice and pretty easy going. The sex was also nice and pretty easy going. He thought the world of Leslie and always treated her with respect. Ultimately, Dave had to move away. And for the first time Leslie thought about leaving Pawnee. But then she realized she would be leaving to get away from the challenges she faced at home. If she was going to move away with a guy her reasons should be to be with the guy. So Leslie stayed in Pawnee and wished Dave well. If more time would've been given she may have fallen in love with Dave because he was a great person and they had similar backgrounds and ideals. However, in retrospect the relationship did lack a bit of excitement.

Chris the MRI Tech- Ann set Leslie up with an MRI tech named Chris. He was arrogant and weird. He insisted that he give Leslie an MRI as she had never had one. Chris declared Leslie had a great uterus that would have enough room for triplets, right off the bat. "Yeah right like that would ever happen! What are the odds of that?" Leslie had thought to herself at the time. Leslie declared the date was over. But before they could part ways Leslie had to take him to pick up his son from hockey practice. That was an awkward car ride.

Justin Anderson\- Justin was interesting. He had an entire lifetime of stories about places and people Leslie could only dream of meeting. But for all of the great stories he told he was not a great listener. They didn't really have anything in common either. Leslie was off put by Justin's personality. They only went out a few times and had never even slept together. The breakup was painless for both but hard on Tom, who was in love with Justin's style, and quiet possibly Justin himself.

Ben Wyatt- Ben was the guy that would randomly enter her mind, from before they even became friends to when she had a full blown crush on him to when they were broken up and she thought it was over forever. After a long cycle of denial, flirting, denial, infatuation, and flirting so nerdy and cutesy it was downright embarrassing the two began dating in secret. It was hot. It was also turning into something real and deep and that's not what is supposed to happen to two people involved in a secret sex scandal. Then Ben broke up with her so that she could run for office and Leslie knew that she was ruined for anyone else. No one else would ever be able to compare. The separation would not last. When Ben resigned so that she could keep her job Leslie knew that Ben was _the one_ and he had been for quite some time. He made her want to come home at the end of the day and actually attempt to balance her work and personal life. He was good and kind and respected her the way a man should respect the woman he loves. She had fun with him in the good times and she had support and balance from him in the hard times. She finally knew what romantic love was and had someone put the effort into caring about her as she did for everyone and everything else.

What Leslie Learned

Leslie learned a lot about herself from the guys she had dated. She learned that she had some (a truckload full) steamrolling tendencies. She needed to be a little less intense. She learned that she was often too quick to think she was in love. Leslie learned that you can't put all your effort into a relationship if it's one sided. She learned that while comfort is essential it can also exist alongside passion. Passion makes for good relationships. Commonality in shared interests and values makes for good relationships. Comfort makes for good relationships. Respect makes for good relationships. You should be with someone that makes you want to be a better person and makes you feel proud. You should be with someone that will make sacrifices for you without expecting anything in return and you would do the same for him. You should be with someone that believes in you and helps you accomplish your goals. He should make you feel prepared to take on the world. You should see love in his eyes when he looks at you. He should be worth the risk.


	2. The Education of Ben Wyatt Part II

The Education of Ben Wyatt Part II

Lilly Thompson\- Ben had a crush on Lilly in 1st grade. She always wanted to share Ben's crayons with him so Ben thought the feeling was mutual because Lilly had her own crayons but always wanted to use Ben's. Then, Lilly started using Kelly Dickson's crayons so Ben asked her why. Apparently, she had only been using Ben's crayons because his box had the built in sharpener so when Kelly got the same kind of crayons she just used Kelly's instead of Ben's.

Kelly Carlson\- Kelly sat next to Ben in fifth grade. They were the teacher's special helpers. He developed a huge crush on her and he thought she might like him too because they got along so well and always had a good time together. But then Kelly confided in Ben that she had a crush on Daniel Peterson.

Ingrid Lindstrom\- Ingrid made Ben feel really good. She laughed at his jokes and listened to what he said. She complimented him and told him he was a great person. They were interested in a lot of the same things. They spent many bus rides talking about Star Wars. After advice from his friend he asked Ingrid to be his girlfriend by giving her flowers he had arranged in the shape of The Death Star and having his friend playing the theme song off a cassette tape. But she turned him down informing him that she had an older boyfriend that was a senior. Ben was very confused and moped around for a bit after.

Cindy Eckhert Cindy was the popular girl in school. Partridge was so small that cliques were rather fluid. While, Ben was considered a nerd and was a bit awkward he could still hang with the popular crowd from time to time, especially because he was involved in a lot of extracurricular activities. Ben had never given Cindy Eckhert much thought until sophomore year. She had always seemed lightyears out of his league but by sophomore year he started to get to know her. They were both in student government and Ben had tutored her in math. She was nice to him and seemed to pay attention to him, especially senior year when Ben ran for and was elected mayor. She declared herself his girlfriend two hours before his inauguration and gave him his first kiss. In a matter of weeks everything in Ben's life had changed. His parents were tolerating each other, he had a girlfriend (who was way more experienced than him and moving things along very fast), and kids that had once ignored him acted like he was their best friend. Cindy moved at lightning speed. Cindy was the first girl he felt up and had taken to a dance. Before Ben had even known what had happened Cindy became the first girl he had sex with. When the first sign of mayoral trouble came Cindy turned Ben down for senior prom. Of course, he destroyed the town and was impeached causing Cindy to publically declare that they were already broken up, which was news to Ben.

Megan Dever\- Ben tutored Megan in math freshman year of college. Ben worked at the tutoring center in college. They would meet in the library. She was always nice to him and he grew to look forward to their tutoring sessions. It was a really nice feeling because he hadn't felt good since prior to his disastrous stint as teen mayor. His confidence levels had been abysmal and he had spent most of freshman year guarded and alone. No one at college knew about Ben's past and while he had looked forward to college as a fresh start he tried to stay under the radar because he feared others finding out. Towards the end of freshman year Ben finally got the courage to ask Megan out. They went on a few dates but then, somehow, Megan discovered Ben's past. Ben was privy to a few whispers and gossip about it but luckily it hadn't spread like wildfire. When Ben asked Megan out on a third date she rejected him in the library and replied, "You know we're not boyfriend and girlfriend right? I'm not interested in that. I think you are and I don't want to go out with you again." In the quiet of the library more than a few people had overheard Ben's humiliation. Ben still had to tutor her for a few more awkward weeks.

Samantha Leistner\- Sam was in Ben's history class sophomore year. They were assigned a project together and became friendly. Ben helped her with a math class, as a friend not as a tutor. They started spending regular time together with class and assignments not even mentioned. They ate together, went to a few school events, and even the movies twice. She thought Ben's nervous awkward stuttering was in her words, "cute." Sam had initiated a few make outs and Ben had initiated a few make outs. Then, one day while Ben was tutoring a freshman Sam walked by him in the library and stopped to say hi. Ben introduced her as his girlfriend. Sam then explained that she was not Ben's girlfriend and didn't understand why he thought so. "But we have gone out a lot and we've made out?" "We made out. So. Are you Amish or something?" The people around them snickered and the guy Ben was tutoring had laughed at him and soon it felt like the whole school was in on the joke.

Claire Lewis\- Claire and Ben had a political science class together and were on the college debate team. She had a confidence that Ben envied. Claire's confidence reminded Ben of how he once use to feel. They had gotten to know each other pretty well and had genuinely become friends. Ben liked Claire as more than a friend if he was honest with himself. But after so many bad experiences concerning girls and people in general he was very guarded. Claire asked out Ben on a date in the beginning of junior year. She had made her intentions clear. Ben was leery at the beginning of the relationship but it wore away. Ben's life seemed to be back on track. He was doing great in school, liked his professors, and had a great girlfriend. His confidence was on the mend as was his heart. By the end of the school year they started having sex. Things were going great. Over the summer they kept in touch. Senior year had them reunited and even dreaming up some plans beyond senior year. They became swamped with classes, assignments, projects, applying to grad school, and internships. Then Claire started an internship and she meant someone else. She told Ben that she had feelings for someone else and it wasn't fair to him. They broke up. It was Ben's first real heartbreak over a girl. In time Ben would come to realize that Claire wasn't as perfect as she seemed. She could be brazen and wasn't always very thoughtful. For instance, when Ben had shared his dream to go back into politics Claire had not encouraged him. She only told him to "read the writing on the wall" and go into the private sector, it paid better anyway. She just didn't get it.

Liz, Jane, Stacy - After college Ben could have gone into the private accounting sector. He would've been sought after and could have been making big money fast. However, the love of government still burned in his veins. His confidence would never be what it once was but he had recovered enough. Matured. It had allowed him to once again dream of his future in politics and he had made a plan for how to get there. He would have to be highly qualified and show that he was fiscally responsible. So Ben set a plan in motion. After college graduation he moved to Minneapolis and began to get his master's degree and work towards becoming a CPA while he worked as a TA and did some tax work during tax season. Liz Nichols was also in the same master's program as Ben. A mutual friend had basically meddled and set the two up. They liked each other and went on a few dates but decided they were better off as friends. That same friend then set Ben up with Jane Weber, a law student. She was 6'4 and as big as a linebacker. Ben felt very nervous around her, like she was hovering over him (she was because of the height and size. It made Ben's mind flashback to when a linebacker put him in a headlock and threw him into a lake after his impeachment). Ben stuttered a lot during the date and almost choked on his food. About half way through the date Jane had made up an excuse and left. Ben later found out that Jane had asked their mutual friend if there was something mentally wrong with Ben. Ben never wanted to go on another set up. However, he got tricked into a set up while visiting his younger brother, who was now in college. It was a double date with Ben's brother Henry, his girlfriend Lacey and her friend Stacy. Ben couldn't get over the name thing. He also felt very uncomfortable being on a date with his little brother and other college students. While Henry was smooth and calm Ben burnt his hand on his dinner plate and knocked over the vase on the table.

Elaine Roberts\- Ben had just gotten hired as a low level government account for the city of Indianapolis. He thought it would be wise to leave his past behind in Minnesota. Moving to a new state and pursuing his governmental goals would make Ice Town seem farther away with less people being aware of it. The job was putting him on the right track and following his plan. He was new to the city and the state. He met Elaine, a tall brunette lawyer ten years his senior. There was something that drew Ben to her. He thought it was silly. She was an older successful lawyer and he never would have thought he had a chance with her. He never would have tried. But Elaine came on to him, in ways that were even obvious to the rather romantically oblivious Ben Wyatt. He couldn't resist and they had a summer romance. But summer romances aren't meant to be lasting. It ended amicably. Ben learned a lot about himself, like summer romances weren't really what he wanted, and he also learned a lot about sex.

Sara O'Malley- Ben quickly became notable in his accounting job for the state and quickly moved up to the budget office. Soon he became a budget specialist traveling all over the state to towns in trouble where he would retool the budget and be met with animosity and a lot of people throwing things at him. After receiving several death threats he was partnered with another man, the always positive Chris Trager. Ben thought there might be a murder suicide. But being on the road with someone creates a bond and it made his job more enjoyable. In between their first and second assignments Ben met Sara. She was a nice woman; tall and brunette and taught elementary school. Chris had goaded Ben into asking her out. Not having a second date with her would've been stupid. Not having a third date, a forth date, a fifth date would've been stupid. The problem was that after six months there was no reason to breakup. But there was also no reason to go forward. It was an easy relationship between two nice people. What could go wrong? Ben actually wished something would go wrong and give him a reason to breakup with her. Ben found it really hard to invest in a relationship when he was constantly out of town auditing. He stopped missing her when he went out of town. Sara was good with the distance but after they had been together for a little over a year she needed to know she wasn't wasting her time. Finally, after many attempts made by Ben to breakup Sara finally confronted Ben. They broke up. It sucked. Ben felt that he would forever be alone and that there must be something wrong with him if he couldn't fall in love with a woman that was perfectly nice. After that, Chris jogged by Ben sitting on a lot of benches alone eating soup. Chris took it upon himself to motivate Ben, be his wingman, and emotional guardian.

Emily McCourt\- Emily and Ben met through playing Risk. She loved Risk as much as he did. She was a chemist. They only went out a few times and talked on the phone a bit (the phone conversation was basically silence on both ends). They had never kissed on the lips, Ben once thought he should kiss her good night but he missed and kissed her chin. Ben discovered that Emily really loved the Star Wars prequels especially because "that guy is so cute". It was such a trivial reason to like the prequels. Ben's respect and likeness for Emily faltered. He tried to tell himself it didn't matter. But he couldn't keep it in. The prequels came up and Ben let it out. He broke up with her. He also thought that her strategy for Risk was rather weak. And it really bothered him that she only wore flip flops, even when it was snowing.

Jamie Wallis Bloomingon Channel 4 News\- Jamie was another one of Chris's set ups. She was a local journalist and the thought of her being a reporter or running a check on him and finding out about Ice Town made Ben even more nervous than usual. At one point he took his shoes off and just held them, in the restaurant. Jamie went to the restroom and never came back. Ben understood.

Lilith Monroe\- Lilith was a self-assured tall brunette that worked in the governor's office in Indianapolis. She was traveled, grew up in Chicago, and "couldn't wait to get out of this hick town". She had zero interest in sci-fi. She thought it was silly. They dated for a few months. Ben was on the road for about 75% of that time. While he was away he did his part to keep the relationship going; calls, postcards, and he sent her flowers a few times. Then one day he got a call that Lilith had seen her ex-boyfriend recently and she was calling to break things off with Ben. She realized that she still had feelings for her ex.

Janet Smith\- Janet worked in the county commissioner's office in Lake County. Chris did everything he could to motivate Ben to ask her out when she had shown interest in Ben. Ben told Chris he didn't see the point since they were only supposed to be in town for a month. "But you never know what will happen. You just have to take a chance. You don't have to marry the girl. Just get dinner and see where it goes. Life is about connecting with other people," Chris kept telling Ben. So Ben rallied up some courage and maybe a dash of hope and asked her to dinner. He just went with it. They went out a few times and slept together and Ben left town and they never spoke again. Ben didn't want to be a jerk so he ended up calling her but she never called him back. It was bit unsatisfying and he didn't see how Chris could be so comfortable with that type of arrangement.

Lilith Monroe Part 2- Eleven months after Lilith had broken up with him over the phone they had run into each at a diner near the statehouse. This led to dinner a few nights later and they started dating again. This time they dated for five months until she once again called Ben and broke up with him over the phone. She had met someone else. Ben felt like an idiot.

Melissa Martinez\- Chris had dated Melissa but then they decided they were better of as friends. They were "amazing friends." Chris decided to set Ben up on a blind date with Melissa. As per usual Ben was not given a chance to say no. Ben felt very awkward, being on a date with Chris's ex. He almost choked on his chicken parmesan three times and got his watch caught in his hair. That was the end of that. When Ben later recalled the story to Chris the man teared up and gave Ben a very long hug.

Cindy Miller\- Chris, without Ben's permission or knowledge, set him up on a date with a woman that worked in the county commissioner's office. Her name was Cindy Miller. Chris had informed Ben that he asked out Cindy Miller on his behalf in front of Leslie Knope, the woman that Ben had developed pretty deep feelings for and who he was pretty sure liked him back. However, Ben and Leslie were going nowhere as a relationship was against governmental ethics rules. It was very awkward. And then Chris called Cindy Miller and made Ben talk to her in front of Leslie and things got even more awkward. Ironically, Chris set up Ben with Cindy Miller because they had something in common, they both worked in government. So Ben ended up getting coffee with Cindy Miller. He had no interest in going out with a woman when he had feelings for another woman. Ben also hated first dates, especially set ups. He spilled his coffee and for some reason used his jacket to wipe up the spill. Cindy was nice so Ben informed her that he was nervous and unbeknownst to Chris he had feelings for another woman and then they parted ways.

Leslie Knope- Leslie Knope was a pain in the ass. But she was a pain in the ass that cared. She had an amazing work ethic that was aspirational. Her faith and belief in government reminded Ben of how he had once felt before Ice Town happened. She was intelligent, compassionate, and so stubborn in her beliefs yet always on the right side of the issue. Slowly, in that his feelings snuck up on him, but rather quickly, Ben most looked forward to seeing Leslie every day. The things they talked about, the way she laughed at his dumb jokes and gave him the benefit of the doubt when he made an accounting pun she didn't get, and how great it felt when they accomplished something together; it all brightened his day. He just wanted to make her happy. Early on in their secret relationship Ben just knew that there would never be anyone else like Leslie in his life. That cold night when Leslie said, "Let's just say screw it", Ben knew she was _it_. And all the mistakes he had made in the past, all the ways he had tried to punish himself, and all the wandering he did trying to make sense of his life; it didn't matter. It had all led him to her.

What Ben Learned

Relationships can teach you a lot. Ben learned that passion, values, interests, and ideals need to be commonalities between both individuals in a relationship. You should miss the person when you are separated but still be able to have an independent side when apart. You need to be able to express what you need and not be a pushover or be passive aggressive. You should want to surprise them and make them smile. You should be proud to be with them. She should give you as much as you have given her, even if it is not all collected at once. She should make you want to be better and work harder and believe in yourself almost as much as you believe in her. When you think of your future you should think of her. You should want to support her and help her makes her dreams come true. She should make you feel brave and bold. The person you choose to be with should hold your hand while you jump off cliffs together into the great unknown. As long as you know that she's holding your hand you know everything will work out in the end.

 _Author's Note:_

 _I was inspired to delve into Ben and Leslie's romantic past by a few different factors: Ben's "I was wandering around everywhere looking of you." Leslie having such horrific breakups but still being so open to love. Both Ben and Leslie being so awkward and such huge dorks that surely they must've embarrassed themselves an infinite amount of times when it came to dating. Leslie is so intense and gives everything to everything and she must definitely do that when it comes to dating which would just be too much for so many guys. And Ben has passive aggressive tendencies but on the flip side can also allow people to walk all over him. I also imagine young Ben, the boy who had the guts and grand idea and follow through to run for mayor must've also had such a grand romantic nature when he was young. We've also seen glimpses of this when it comes to Leslie. So I wanted to explore how their romantic past shaped what they learned about relationships as they matured and how it led them into being in the right place when they found each other. I got the title from hearing Mike Schur say that The Education of Leslie Knope had been in the running for the title of the show. I included all the numerous breakups and relationships Leslie has referred to over the course of the show. I also tried to include lots of weird names and Midwestern names and names of Swedish origin etc. It was also really important to me to include Leslie's relationship to sex. I like how the show makes it seem that Leslie can be a bit old fashioned, proper, and naive in some ways when it comes to sex and how she seemed to not have a confident and positive relationship when it comes to sex but is still curious about it. I imagine she and Ben would hold in common a lot of the same feelings on sex. Of course, Ben and Leslie together seemed to never have any qualms about sex and certainly enjoyed themselves._


End file.
